Come Out and Play
Elliot Silvestri
Come Out And Play
A Male Chastity Erotic Novel
Elliot Silvestri
This is a work of fiction. All of the characters, organizations, and events portrayed in this work are either products of the author’s imagination or used fictitiously. Any similarity to real persons, living or dead, is coincidental and not intended by the author.
Come Out And Play
A Male Chastity Erotic Novel
Copyright © 2022 Green Bush Publishing
First Edition
All rights reserved. No part of this work may be reproduced or transmitted in any form or by any electronic or mechanical means, including photocopying, recording, or by any information storage or retrieval system, without the written permission of the publisher.
A Green Bush Publishing Book
The characters and events portrayed in this work are fictitious. Any similarity to real persons, living or dead, is coincidental and not intended by the author. Contains adult material that might not be suitable for all audiences. This work is a fantasy; in your own life be sure to follow safer sex practices.
All characters depicted in this work of fiction are 18 years of age or older.
Contents
Prologue
Chapter 1
Chapter 2
Chapter 3
Chapter 4
Chapter 5
Chapter 6
Chapter 7
Chapter 8
Chapter 9
Chapter 10
Chapter 11
Chapter 12
Chapter 13
Chapter 14
Chapter 15
Chapter 16
Chapter 17
Chapter 18
Chapter 19
Chapter 20
Chapter 21
Chapter 22
Chapter 23
Chapter 24
Chapter 25
Chapter 26
Chapter 27
Preview
About the Author
Book 1
Prologue
I couldn’t help myself. My eyes automatically fell to Kris’s ass as she led me through the halls of the office.
Her ass was pleasantly big and round. Maybe the skirt she was wearing was a little too tight or maybe she had put on a few pounds recently, either way I didn’t mind.
Since I was coming to the end of my probationary first year at the investment bank with the clever moniker of Consolidated Investments and Financial Advisors, I figured she had summoned me for some paperwork. Ms. Taylor, as she liked to be addressed by everyone who was her subordinate, always had a frown on her face and never looked happy.
Oddly, that was a turn-on to me; I had a thing for older women. It had started in high school and went with me to college. I had tried bedding a few of my teachers but never with any success. Out in the workforce, I had hopes that my charm and good looks would take me further into the bedroom of these experienced and worldly women.
The HR office was a cold and unpleasant place. I was mildly surprised to find Rebekah in the office. She was my immediate boss, or at least I reported to her. I hadn’t been so bold as to try to seduce her, but given half an opportunity I would have gotten her drunk and done whatever necessary to sneak into her panties.
Ms. Taylor indicated a chair for me to sit in. On the desk in front of me was a plain manila folder that seemed to contain only a few pieces of paper. A new contract?
The HR head indicated the folder. “Please read the document.”
With a shrug I opened the folder and started reading.
Two seconds after I did, my heart sank and my stomach tightened. I was certain I was going to throw up.
I’d love to fuck Strohman.
Mouth cunt ass.
I don’t care.
Maybe the ass.
She’s got a nice cake.
She probably loves getting buggered.
I didn’t need to read beyond that.
Immediately desperate, I tried anything that might work. “This…this was a private email conversation.”
“Conducted on a company computer through the company’s internet, and on company time according to the time stamp,” Ms. Taylor said coldly. “Judging from your reaction you’ve confirmed this is your writing.”
“It’s…it’s…”
I knew exactly what it was. A conversation with a few friends from college. The email thread veered wildly between sports, sex, alcohol, and drugs. The emphasis was on sex. Mostly who we’d like to fuck and how we’d like to fuck them.
“Dylan Beemis, your probationary employment is being terminated immediately,” Ms. Taylor went on. “You will not be given a positive recommendation by any member of this organization.”
“Wait!” I was desperate. “I can explain.”
“Can you?” asked Rebeckah. It was clear that she believed I couldn’t.
“It’s not what you think it is,” I said, stalling for time.
“What is it then?” This was asked by Ms. Taylor. She was skeptical.
“I’m writing a movie script with some friends and what you have here is the rough draft.”
The lie fell flat on my ears. Dylan couldn’t imagine what it must have sounded like to the two female managers.
“You have to believe me,” I begged, darting my eyes back and forth between them.
I would have fucked either of them right then and there to make them believe me.
Hell, I would have fucked either of them at any time for any reason. They were both sexy, older women.
Even as I was getting fired, I was rock hard in my pants.
Fuck!
“No, we don’t,” said Ms. Taylor. She went to her office door and opened it. One of the not-so-subtle security guards the company employed stood there. I was being escorted out. “Your personal belongings will be delivered to your home address we have on file. Is it correct?”
I had no idea if it was. I had been hired by CIFA right out of college. I hadn’t yet been there a year. I had nothing but huge student loans and no prospects now.
Fuck!
“Yes,” I said, fighting back the tears I could feel coming. It was either cry or punch someone.
I didn’t want to do either.
Fuck!
The hired goon walked one step behind me all the way to my car. The overpriced car I had bought with my first paycheck. Maybe a BMW wasn’t super luxury, but my mother had never had anything better than a ten year old new-to-you Chevy. Now it was going to be repossessed in a month.
As I got into my car, the goon blocked the door from closing. He reached in and pulled the sensor off the windshield. I’d no longer be able to drive into the parking garage. The ID and passcards on the lanyard around my neck were assuredly already deactivated.
I drove away and got all the way to the gas station on the corner before I pulled over and started crying.
Chapter 1
The Rat Trap was the sort of bar young up and comers frequented. Well, young up and comers like my former self along with those who wanted to attach themselves to young up and comers like leeches.
I’d fucked a few of the women who were looking for a husband who could support them in luxury. Yes, I was making a ridiculous amount of money for a first job out of college, but it was a job I hated and it wasn’t doing anything fancier than using computer applications to predict where the next flash in the pan investment opportunity was. I was good at it, but I hated it.
I took home my fair share of women from the Rat Trap. If I wanted to I could have taken home some of the men as well.
But I only ever fucked those women once for two good reasons.
First, I wasn’t going to let myself get trapped by some gold-digging whore.
Second, most of those that I fucked her less than impressed with my non-stellar cock.
I’d measured it more times than I care to remember in high school and college. At best, I was packing four thin inches.
Women aren’t impressed with that, even if they say they don’t care.
Fuck ‘em. I had spent more than my fair share of time in the gym and running to get myself into shape. I wasn’t going to be winning any Olympic medals, but I wasn’t ashamed to take off my shirt.
I was ashamed to take off my pants, however.
I got too drunk too quickly and invited Lydia home to my place.
She laughed and offered to drive because I was in no condition to get behind the wheel.
The Rat Trap was happy to keep cars overnight. I wasn’t worried.
She drove me to my place.
High Gate Tower. Again, not top of the line luxury, but more than respectable. I was paying more than I should have for the apartment, but it was twice as big as any trailer or Section 8 housing my mother could ever afford. The view was okay, I was only halfway up the tower.
When we walked into the overly ornate lobby, the doorman gave me a dirty look. Probably gave the same look to Lillian. Still, he recognized me and allowed us in. I’m sure he’d be glad when I got evicted. In my drunk state I didn’t give a shit.
As we waited for the elevator I leaned into Lucy. I think she was keeping me upright. I watched the numbers slowly descend to the lobby. Before we could get on, the rider had to get off.
Heh. Get off.
I’d seen her before. An incredibly beautiful ice cold blonde. I couldn’t see her eyes in the dim light, but I was certain they were baby blue. My cock stirred in my pants. She was someone rich or important because she lived on one of the upper floors. I eyed her without making it seem obvious I was checking her out. Looking back, I was probably way too obvious about it. Still, she had a nice rack and an excellent ass. She was in the Goldilocks zone, neither too big nor too small.
I remembered to step aside to let her out.
I checked out her ass as she left.
Leah pulled me into the elevator and wisely said nothing about my indiscretion. Instead, she kissed me. She was more than pretty enough, but I could see the dark roots to her dyed-blonde hair. She had brown eyes. Her skin wasn’t pale enough. Pressed up against her I could tell her tits were too small. She let me grab her ass. Nice athletic body, though.
“Wow, nice,” Lydia said when we finally made it to my apartment. My soon to be ex-apartment.
“Thanks,” I said as I staggered to the couch and collapsed on it. She looked out at the cityscape another minute before turning around to look at me.
“How drunk are you?” she asked.
“Drunk enough to make bad decisions.”
Lynn laughed. “I mean…are you so drunk that you can’t get hard?”
“What?”
“Aren’t we going to fuck?”
“Sure!”
She joined me on the couch and we started making out. She was thinner than I liked. Small ass and tits. Almost immediately she straddled me and I was certain she was going to be disappointed.
Still, I kept going, pulling up her skirt to reveal her ass. My hands went to her cheeks. They were bare because she was wearing a thong. Of course she was.
“You aren’t hard,” she said, breaking our kiss.
“Too much whiskey,” I lied. I was hard. My cock was just small.
“If you tell me your ultimate fantasy I’ll make it come true tonight,” she whispered in my ear and added a giggle. Her hand got between us and she groped for my cock. “Oh.”
She was obviously disappointed by my smallness.
I was used to it.
I expected her to leave.
“Sorry,” I muttered.
“I can fix that,” she said and moved down my body to give me a blowjob.
I just stared at the top of her head, studying the line of dark hair where she parted it. For her part Linda unbuckled my belt, lowered my zipper, and pushed down my pants and boxers just enough to free my cock.
My small cock.
My cock that was partially erect.
I think I was sobering up because when I got really drunk, I couldn’t get hard at all.
Lisette didn’t comment on my smallness, she just lowered her mouth to my semi and started sucking.
It felt good to have her warm mouth around me, but it was only partially effective.
Maybe her pussy was so well-fucked over the years that she was loose enough a bit of floppy flesh could penetrate her.
I didn’t hold out my hopes.
She made a valiant effort, but after five minutes, eventually stopped and looked up at me.
“Sorry,” I apologized. “Whiskey dick.”
She gave me a little smile, climbed off my lap, and, after standing up, proceeded to pull her shirt up over her head along with her bra.
Her tits were great. The left nipple was pierced. I liked that. The little silver balls on either side of the light brown flesh was a visual high point.
It barely affected my cock.
She leaned forward. I cupped her small tits in my hands. Layla whispered in my ear, “Tell me what your ultimate fantasy is and I’ll make it come true tonight. Want me to swallow your load? Fuck my ass? Spank me?”
I laughed a little and ruefully shook my head. I was drunk and stupid. “I want you to tie me up and ride me.”
She smiled and gave me a little grin. “Kinky. I like it. But I didn’t bring my bondage gear with me.”
The stupid smile on my face told her everything she needed to know about me. “I’ve got a bunch of stuff in the bedroom.”
And so we went into the bedroom.
I dug out the restraints I had bought with my second paycheck and never had the opportunity to use. All I wanted was an attractive older lady to tie me up, spank my ass, and treat me as her sex slave. Was that too much to ask?
Lauren had me strip. That was only fair since she was already topless.
It took some time and effort, but eventually we got the restraints worked out and soon enough I was spread-eagled on my bed, wrists and ankles tied to the thick corner posts that I knew I needed when I bought the damn thing. I felt vulnerable.
That was what I needed because when I realized I couldn’t free myself, my cock was rock hard.
If only I was longer than four inches.
My size didn’t seem to upset Laila all that much. She lounged next to me on the bed and idly stroked my muscular chest and legs, but only allowed herself the slightest of touches to my straining cock.
“It’s so cute,” she finally said, crushing my ego and making my small cock strain all the harder.
She laughed at me. “Look! He’s trying so hard to get bigger!” She giggled some more. “Trying harder.”
“I’m sorry,” I apologized. I was still drunk but not so drunk that I didn’t know what I was doing. I hated myself and loved her humiliation. “Are you still going to fuck me?” I asked desperately.
Lauren gave me a quick kiss on the lips. “I’m going to fuck you good,” she said.
She was still wearing her skirt and her small tits jiggled around pleasantly as she sat up and straddled my legs. I breathed heavily as she ran her finger from the base of my cock up to the tip where she circled the corona before pulling it away.
I groaned in frustration.
“Tell me you like to eat pussy,” she said.
“I love to eat pussy!”
She laughed and spun her body around, repositioning herself so that she was now straddling my face. I looked up between her legs. Her thong was bright red and hid her pussy away, but I could smell her. Lifting up my head I tried to lick the lace that covered her sex, but she was just out of reach.
Before I could beg to taste her, I felt her lips wrap around my manhood and I moaned at the surprise. She then lowered her pussy to my face and I started licking like it was going to save my life.
It was equally frustrating trying to lick her savory pussy as it was getting a blowjob from her. She could easily deepthroat me. That wasn’t any trick. But when I started getting worked up and close, she would immediately stop sucking. I knew it was a tease but it was frustrating, which was the point, I suppose.
In one of her pauses she said, “Okay, make me cum first and then I’ll let you cum.” Lauren reached back and pulled aside her thong giving me full access to her delicious pussy. I licked and sucked in a desperate need. She rode my face. It was an even exchange.
“Oh fuck. Oh fuck. Oh fuck! OH FUCK!” She screamed out as she came. She came hard. Her body shook. She sat down on my face, smothering me. There were worse ways to die.
I didn’t die.
As she rolled through her orgasm, I realized that Lillian wasn’t just wet from her amrita and my saliva, she was sopping wet. Dripping. Her taste went from pungent to salty and bitter.
“You’re drowning me!” I complained to her, my words mostly muffled by her pussy and ass.
Layla giggled and lifted up her ass. “I'm sorry. I should have told you I was a squirter.”
I swallowed and tried to clear the sharp taste out of my mouth. “It’s fine.” It wasn’t fine but I was willing to suffer through this to cum in her mouth. “I think you made a promise?” I reminded her.
“I did,” she said as she ran her finger down the underside of my cock with just enough pressure that I could barely feel it.
I groaned.
“Please,” I begged.
She laughed and got off my body. “I didn’t say when I would make you cum.”
“What?!”
Lucy gave me a wink as she pulled her thong back into place. I thought she was going to leave me, but instead she bent over and licked the length of my cock, which gave me hope, but then she pulled away again.
“I’m a liar,” she told me.
“Please, just free my hand so I can jerk off.” There were tears in my eyes. I was right on the verge of cumming and I would do anything to make that happen.
“No.” She tilted her head to the side. “Do you have any toys?”
“Toys?” I was confused. I had left all my childhood toys, what few there were, behind at my mother’s apartment.
“Sex toys? You’ve got the restraints, surely you have something special for a lady in need of assistance. I mean, you’re a good looking guy, but when you take off your pants—” she flicked my cock and I yelped in surprise “—I’m sure you’ve disappointed more than one girl.”
I sighed and indicated my dresser by inclining my head. “Bottom drawer.”
With a skipping step, Lainey went to the dresser, dug among my t-shirts, and pulled out an impressively large vibrator I had used on a couple of different women. They still didn’t want to see me after one date.
“Compensating for something,” she asked archly.
“No.”
She found the switch and turned it on. I buzzed pleasantly. Her grin grew. “Ever shove this up your ass, after the lady left?”
“No!”
Laura proceeded to straddle me again, this time staying up on her knees. Hiking up her skirt, she pulled aside her thong again and plunged the vibrator up her pussy.
I watched, fascinated, as she masturbated, putting on a show for me. Just watching made my cock twitch. If she sat down on my hips I could make a couple of determined thrusts. That would have been enough to cum, even if I was just rubbing it on her ass or thigh.
But Liana stayed on her knees, even as she was cumming. She came hard, again. She squirted again. I had never been with a squirter before. I was sure I smelled piss.
“Huh. Wow.” She tossed the pink vibrator next to me and sat on my thighs, careful not to touch my cock. “Now what?” She wiped her sweaty forehead with the back of her hand.
“Now you’re supposed to make me cum,” I reminded her.
“Right.”
She got off the bed and went to my closet.
“What are you doing?” I called to her.
She didn’t reply but a few seconds later she came out of the closet with the one suitcase I owned. I had rarely used it over the past year when I had started my job.
“Put that back,” I said, annoyed. I hadn’t figured out what she was doing yet.
I was stupid.
Leona didn’t say a word to me as she exited the bedroom with the suitcase. I could hear her moving around in the living room, banging things around.
“What are you doing?! Come back here!” I called and begged for her to return, but she took her time, only coming back after maybe five minutes.
My cock, stupidly, was still hard. She looked at it and flicked it with her fingers. I winced. She laughed.
“Nice watch,” she said. I had removed it before we had tied me up to the bed. It wasn’t terribly expensive, but I liked it. As I watched she tossed it in the suitcase where I spied my Xbox and laptop.
“Are you fucking robbing me!?”
“You catch on fast.”
I had an iPad on my dresser that she took as well. She left me my cell phone. “These are such a bother to get rid of. I’m sure it’s registered and all. I know a guy who can break it down, but it’s such a pain in the ass.” She put it back down and I breathed a sigh of relief.
“Please, don’t rob me. I can give you money. I need that stuff for work.”
Lyra scoffed at me. “You told me you just lost your job,” she said. “You really shouldn’t drink so much.”
She found my pants and pulled out the wallet. I didn’t have that much cash, but she took the two credit cards I did have.
“Don’t,” I begged. “Please, I’ll pay you!”
“I’m no whore!” she cried, offended, and then gave me a wink. “I did promise you something.”
My cock was still hard. She was robbing me and I was still hard.
Fuck!
Leslie gave me a couple of licks to make sure I was good and hard. Then she gave me the worst handjob ever. She jerked me with a staccato rhythm and kept pausing at the wrong time.
“Are you almost there?” she asked.
“Yes,” I sobbed.
“Good.”
She continued her handjob even as I held back. She was very good at what she did. She got me right up to the edge…and then stopped. She did that multiple times. I just wanted it to be over.
And then she did it again. I was hyperventilating. She watched with disinterest as my cock bobbed and jerked…
Finally I came. I shot my load all over my stomach.
“Wow,” she said. “That’s a lot more than I thought you could make.” She trailed her finger through the puddle of cum on my skin and brought it up to her lips, but stopped before tasting it. “You don’t think I’m going to taste this, do you?”
“No.”
“You’re going to,” she giggled.
“No!”
“Taste yourself and I’ll free you,” she promised.
Liv held her finger just in front of my lips.
“No.”
She shrugged. “Your loss.” Picking up her bra and top she got dressed as I watched, my dread and desperation slowly growing.
“Okay, okay,” I relented. “I’ll do it.”
Once more she laughed at me. “I knew you would.” She came back to the bed, dipped her finger in my cum that was now starting to slide down my side and offered it to me.
I tentatively licked her finger. It tasted vaguely of salt and bleach. It wasn’t awful, but it wasn’t good.
Lara laughed at me. “I can’t believe you did that! You’re such a sucker!”
“You said you were going to free me!” I knew now I had been duped.
“I didn’t say when.” Without another word she disappeared into the bathroom. I heard water running in the bathtub. A moment later she came. I could still hear the tub running. “Someone will be by in a while to free you.”
“What’s that supposed to mean?” I asked.
Once more she smirked at me. “Apartment buildings generally don’t react well to flooding. By the way, it was piss. I don’t squirt.”
“No! Don’t! Please!” I blurted out, but she was already leaving the bedroom with my suitcase in tow. A moment later I heard her slam the apartment’s front door.
I was fucked.
Chapter 2
I screamed and yelled for a few minutes, until my voice went hoarse. I knew the walls of the building were nearly perfectly soundproofed; they were completely different from the apartments I lived in with my mother where I could hear televisions, fights, and sex all the time.
My place was nice. No one was coming to my rescue…not until the tub overflowed and flooded the apartment below.
Fuck.
I could hear the water running and that immediately went to my next problem. I needed to piss.
Right now I knew I could hold it, but not forever. I tried to figure out what time it was, not that it mattered.
After midnight? Three A.M.? No clue.
I was going to get fucked on the damage to my apartment and the one below and I had no job.
I started laughing.
I started crying.
I was incredibly angry that Luba had pissed on me. Pissed in my mouth.
Fuck.
I tried to sleep. Maybe I did a little.
When I realized I was awake, I heard water running, I could just see the water soaking the bedroom carpet. My bed was wet.
It wasn’t from the water. I had pissed myself while sleeping.
I hadn’t done that since I had last gotten blind drunk.
Fuck.
At least my bladder didn’t hurt any longer.
It was morning. I could see light coming through the blinds.
I tried calling out again.
Nothing.
It was well into mid-morning when I finally heard my front door open.
“High Gate Towers security,” a man’s voice called. “Mr. Beemis, are you here?”
“In the bedroom!” I called out. I was done. I didn’t care who saw me tied up and naked on my bed, covered in piss and cum.
A tall guy looking like an ex-cop shouldered into my bedroom. He saw me on the bed and grinned. “Have a wild night?” he asked.
“Could you untie me?” I asked desperately.
Instead of answering, the security guard just moved into the bathroom, squishing through the sopping carpet. Finally the water stopped running.
He reappeared a second later and glared down at me. I saw his eyes glance at the dry blanket shoved to the foot of the bed, but he didn’t cover up my shame.
“Would you mind covering me up?” I asked as politely as I could.
“No.”
“Well fuck you very much,” I said. “Would you please cut me free now?” I was fucking frustrated.
Instead of answering me or untying the restraints, he instead looked to my bedroom door.
I followed his gaze.
The ice queen from the elevator was glaring at me. Or maybe she just had a particularly bad case of resting bitch face.
She was dressed in an office-appropriate skirt suit. That alone was enough to give me an undeserved hardon. Add her blonde hair, blue eyes, big tits, and generous ass to the package and I was standing up in all my glory.
Again.
It wasn’t that much glory.
I saw her eyes take it all in.
She wasn’t impressed.
“Care to explain what happened here last night, Mr. Beemis?”
“Do I have to?” I asked lamely.
“Yes.” It was an order.
I loved taking orders from icy bitches, though I’d never admit it to anyone.
“My arms are starting to go numb,” I said lamely.
The guard looked at the blonde. She nodded once. He set to work untying me. As he did so I explained everything, my words tumbling out faster than I wanted.
She was impassive the entire time. The guard said nothing.
When my arms and legs were free, the guard backed away.
“Please call a maintenance crew, Mr. Samson. Have them put this apartment back to order.” Shifted her gaze to me as I sat up, carefully keeping the sheet over my cock. “It is with some good fortune for you that the apartment below was being renovated. The contractor noticed the water damage and…here we are.”
“Do you mind turning your back so I can get dressed?” I asked her.
“I mind very much because when I checked your lease, it appears you do not have any renters insurance.”
Why the hell had she checked my lease before checking on my apartment? Fucking bitch.
I wanted her so badly. My cock wouldn’t go down at all. I hated myself.
“Yeah…I don’t have any,” I said. What else could I say at that point?
“It is in your lease that you are legally required to carry liability renter’s insurance.”
“So evict me,” I stupidly said.
She just kept her eyes focused on me.
“You’ll pay for the damages,” she said.
“Joke’s on you. I don’t have a job. I got fired yesterday.” I started giggling.
The Ice Queen was unamused. “Would you like to file a police report?” she asked.
That question made no sense. If anything, I was in the wrong over discussing my bosses and wanting to fuck them.
“I don’t think a police report is going to get my job back.”
“I meant for the woman who robbed you.”
“Oh. That. Right. Yeah, I don’t even know her name. Something that starts with an L. Lydia. Layla. Lucy. Lillian. Leticia. Larissa. I don’t know.”
“You picked up some floozie at a bar, brought her home to fuck her, and she robbed you.”
I grinned. “Yeah, that about sums it up.”
“Well, Mr. Beemis, it seems like you are well and truly fucked.”
I started laughing and it took all of my self-control not to let it get hysterical.
“Yeah, that would be correct.”
She produced a business card from nowhere and placed it on my dresser. “Get yourself cleaned up and dressed. I would like to speak to you in an hour.”
With that, she disappeared out the door.
“What the fuck?” I asked myself.
The security guard, Mr. Samson, reappeared. “I suggest you do as Ms. Daggett said,” he rumbled in his deep voice. “Hell, I’d suggest you do it because you smell like piss.”
I wanted to order him out of my apartment. But instead I walked to the bathroom with a sheet wrapped around my middle like some perverted diaper.
I needed a shower. My life outlook was only slightly better when I was done.
The carpet was still soaking wet, but I got mostly dressed and brought my shoes and socks out to the living room.
Mr. Samson was still there.
“What the fuck are you still doing here?”
“Waiting for the maintenance crew. And making sure you go to Ms. Daggett’s office.”
“I’m going to eat something first.”
I was starving.
I had just put a bagel in the toaster when the maintenance crew appeared. Mr. Samson let them in. I didn’t acknowledge them. I’m pretty sure the two guys, roughly my age, gave me knowing smirks.
Mr. Samson watched me as I ate. I tried to ignore him. When I was finished, he said, “Time to go.”
“Go where?” I asked innocently.
“To see Ms. Daggett. Now.”
I had nothing better to do with my life at the moment. Plus I was intimidated by the man. I had no trouble admitting that.
I was happy to leave but I didn’t know where to go exactly. I asked Mr. Samson. “Her office is on the twenty fourth floor.” He pointed to the ceiling.
I knew the tower had twenty five floors. I liked Ms. Daggett’s confidence.
Mr. Samson escorted me to the elevator and used a key to allow the elevator to go to that floor. I had always ignored the upper floor buttons because they were locked out. I knew they weren’t for me.
I was only mildly surprised that Mr. Samson didn’t escort me to Ms. Daggett’s office. He left me alone in the elevator. I was completely surprised that the elevator opened directly into the office. The office seemed to take up most of the twenty-fourth floor of the tower. My apartment only took up a quarter of my floor.
What was even more surprising was that Ms. Daggett was alone in her office, sitting behind a large black glass table, working on a laptop. When the elevator doors opened I automatically stepped out, but didn’t know what to do then. She didn’t acknowledge me and I didn’t want to interrupt her work.
I just stood there and stared at the beautiful businesswoman working at her desk. She was yards away but I could tell she was a natural blonde. I could just see the top edge of her cleavage. I managed not to get an erection over that. I tried not to think about her sitting on her shapely ass. The suit she was wearing was typical business navy blue, but she wore black stockings, and practical heels. Her white silk blouse said sexy and business in the same breath.
I wanted to fuck her.
She was older. I loved older women. I couldn’t say for sure how old. At least thirty. Probably forty.
I loved that she was making me wait, but it wasn't like I had anything better to do with my time.
Finally she looked up at me. “Dylan,” she said, her lips frowning. “Dylan Beemis.”
I stepped forward and stopped. “Yes. That’s me.”
It was something stupid to say. Of course it was me. She knew everything about me.
Ms. Daggett indicated a chair in front of the table that served as her desk.
I sat.
She just started talking. No introduction. “I just confirmed with Consolidated Investments and Financial Advisors that you are no longer employed there. According to your lease application, you have no other source of income. You have an expensive car, a BMW, in the Tower’s parking garage, that you no longer have the means to make payments on the lease. You’ve recently been robbed. You have no assets other than a tiny 401(k) plan.” She glanced at my crotch when she said tiny. I was sure of it. “Your apartment recently suffered serious water damage due to negligence on your part which also damaged the apartment under yours. You have no renters insurance and have no means to pay for the damages. Does all this sound right to you?”
“Uh…I’ll pay you back,” I said. “I’ll be able to get another job.”
It was a lie and she knew it.
“Consolidated Investments and Financial Advisors has essentially blackballed you from the investment and banking community. You were let go for reasons of sexual harassment. I confirmed that with their HR. Are you going to work at some fast food joint to pay us fifty thousand dollars in damages?”
I nearly passed out at the mention of the money.
Fuck.
“I…I don’t know.”
I wanted to put my head between my knees and just breathe so I wouldn’t pass out. Maybe passing out would be a good way to get out of this inquisition.
“You have several problems in front of you, Mr. Beemis, and no way to solve them.”
“I know.” I was on the verge of tears. I didn’t want to cry and prove to her I was a pussy.
“I might have a solution for you,” she suggested.
I blinked. “You do?”
“You are young and handsome and apparently skilled enough to bring many ladies back to your apartment, though there are none who return apparently.”
“How could you know that?”
She smirked at me. “Security cameras are installed in all the elevators and hallways. We reviewed the ones on your floor going back several months.”
“Oh.”
“Unfortunately, you have a small cock.”
I jumped up. “How could you possibly know that?”
“I saw it this morning,” she said drily. “At full staff, sadly enough.”
“Oh.” I sat down.
“But I feel you have some potential. I’d like to offer you a job.”
I blinked. “What?”
“I’d like to offer you a job,” she repeated.
“Doing what? I did finance at my old job—”
“Personal assistant,” she interrupted me.
“Assistant? That’s not what I want to do.”
“You’ll be paid as much as your old job. You’ll live here in the Tower rent-free.”
“That’s a pretty good deal,” I mused as if I was negotiating a deal. I had nothing and she was throwing me a lifeline. I had no idea why, but I was flirting with danger by not immediately accepting.
“It is,” she agreed and slid a sheaf of papers across the desk to me. “This is your contract. Read it and sign it.”
I immediately grabbed a pen off her desk and flipped to the last page, looking for the “Sign here” yellow sticky.
“Read it first,” she warned me.
“Why? I don’t have any choice.”
“We always have choices, Dylan. The personal assistant is only a title. You’ll be doing other things for me, if you read the contract you’ll find out all the details.”
“What other things?” I was nervous. This sounded like a trap into illegal activities.
“Sexual services. Stand up and strip off your clothes,” she said coolly.
“What?” My pen was hovering over the dotted line.
“Stand and strip. The contract specifies I can use you for any purpose I want, sexual or otherwise.”
My small cock was immediately hard in my pants. My face was flushed. I wanted this more than anything in the world, and yet somehow I managed to keep a logical head on my shoulders. That shouldn’t have happened.
“You want me for your sex slave? That’s…basically illegal, isn’t it?”
Her smile was thin. I wanted to kiss her lips when she pressed them together tightly like that. “The contract is basically unenforceable, but then I’ll just stop paying you and you’ll be right back where you started. Strip.”
I literally had nothing to lose. I mean, maybe she could have me arrested for some perceived crime of getting naked in her office. I was sure there were cameras in the office. I was equally sure she didn’t have time in her busy and important life to play stupid games with me.
Unless she liked playing games with me.
I stood.
I slowly stripped.
I didn’t make a show of it. I wasn’t in some gay nightclub. I just undressed like I was in the gym locker room.
She pushed back from her table and uncrossed her legs. I wanted to watch her play with her pussy while I undressed, but she didn’t do that. She just watched.
I hesitated when I was down to my boxers. I was making a small tent inside them. I had already kicked off my shoes and tossed all my other clothing on top of them.
“All of it,” she said. “I want a full inspection of what I’m getting.”
I dropped my boxers.
My cock was trembling with every heartbeat.
Ms. Daggett stood up from her chair to get a better view.
Her lips curled into an amused smile. She circled around the table and approached me.
“Keep your hands at your sides,” she told me as she slowly circled me. I felt her fingers touch my back just above my ass. I shivered in anticipation of what she could do to me.
Her fingers continued from my back to my hip and then just her index finger traced a line barely above the top edge of my pubic hair before she pulled away.
I so desperately wanted her to touch my cock but I didn’t dare ask for that privilege.
“Do all your hook ups flee your bedroom when they see your small cock?” she asked, leaning back against the black glass table. I envied it because she rested her ass on the smooth surface. I wanted her to sit on my face.
“Not all of them.”
“But you’re so small,” she pointed out, literally pointing at my cock, hard and erect and not more than four inches long. I knew how long it was. I spent too much time in high school and college measuring it.
“I know.”
“You have a beautiful face and wonderfully muscular body, lean and athletic without being muscle bound, but that cock…” She trailed off and clicked her tongue. “Such a tragedy, but maybe we can do something about it.”
I had no idea what she was talking about. I was a realist. No pill or surgery would make me bigger.
“What do you want me to do?” I asked.
She didn’t acknowledge my question. “If you trimmed your hair, it would look bigger at least. Did you know the ancient Greeks admired men with small cocks? Large penises were considered animalistic and were undesirable. Or maybe Greeks just have small cocks in general. Do you have any Greek blood in your veins, Dylan?”
“I don’t think so…”
“I want to watch you jerk off,” she said abruptly.
We both looked at my hard cock.
“I can do that,” I said, but uncertainty was in my voice.
I didn’t move. She lifted a foot and she touched my ball sack with her pointed shoe. She bounced it lightly. I loved her touch, even if it was abusive.
Especially because it was abusive.
“Do it or I won’t have you sign this contract,” she said, tapping the papers next to her.
I moved my hand and started jerking off. I knew it wouldn’t take long.
Ms. Daggett moved away. I didn’t look at her because I didn’t want her to think I was some creep getting off on her beauty, even though that seemed more than obvious at the moment.
“Don’t cum yet,” she cautioned me.
I slowed down.
A second later I saw her hand holding a silver platter enter my line of sight. I was watching my cock because I was afraid to look at her.
“Don’t make a mess on my floor,” she said. I noticed the floor was a beautiful dark hardwood. Easy to clean up cum from, it wasn’t like it was a carpet.
But I didn’t want to piss her off.
“Okay,” I grunted in agreement.
“Down on your knees,” she ordered me. “Put your cum on the platter. Don’t make a mess.”
I was starting to get her kink. She wanted to control me. I wanted to be controlled. It was perfect.
I fell to my knees. She resumed her position leaning against the table. Her legs were slightly parted. I couldn’t help myself. I had to look up her skirt.
She glared down at me when I did so. I didn’t stop jerking off. She didn’t close her legs. I was certain I saw a flash of pink between her thighs.
That alone was enough to make me cum.
I groaned loudly as my hand stopped pumping and thick white ropes shot out of my inadequate cock. I managed to land it all on the large oval platter. It had to be some overly expensive bit of servingware or maybe a family heirloom.
I liked the idea of soiling her grandmother’s wedding silver.
My orgasm’s result lay splattered all over the platter. I was rather pleased with myself.
“Such a large amount,” Ms. Daggett commented. “I wouldn’t have expected so much…but your balls appear normal, if not your cock.
“Th-thanks?”
“Please don’t leave a mess on my platter,” she said.
“What?”
“Clean up your cum.”
I looked around for a bathroom door or maybe some tissues to wipe up the cum I had left behind. Why the fuck had she had me cum on the silver platter if she was just going to have me clean it up immediately anyway?
“Where’s the bathroom?” I asked. “A towel?”
Her smile turned evil. My cock suddenly shrank at a rate I didn’t think was possible. “Use your mouth,” she said slowly.
My balls wanted to pull back into my body.
That was why she wanted it cleaned immediately.”
“You…you’re kidding, right?” I asked, both nervous and turned on. This wasn’t a humiliation I had been expecting.
“No. If you had read your contract,” she tapped the pile of paper next to her, “you would understand that I get to control your every little sexual action. Clean up your mess or you’ll be paying for the damages to your apartment.”
Lots of women and plenty of men swallow their male partner’s cum all the time, every day. Lots of men ate their own cum. I knew that. But I couldn’t make myself do it. I just stared at the mess I had made on the platter.
Luckily Ms. Daggett helped me along. Her pointed shoe snaked in between my thighs. It wasn’t exactly a kick but it sure as hell felt like one. I doubled over in pain.
I wasn’t into ballbusting until Ms. Daggett kicked me.
I loved and hated it.
“I understand your reluctance, but if you don’t do me this service, well…you know the consequences.”
I wanted to throw up. Anyone who has been kicked in the nuts knows what I’m talking about. At that point I figured if I threw up, I threw up and my life was already fucked, what’s a little puke on the floor as well?
Reluctantly I lowered my face to the platter. I could smell the acrid chemical scent of my spunk.
I licked it up.
It was terrible.
It wasn’t as terrible as I thought it would be.
I swallowed as much of it as I could without tasting it.
I felt my little cock getting hard again.
Why the fuck was this turning me on?
The hard part was chasing the little clumps around the platter with my tongue. Cum was slippery enough that it was difficult to trap. Eventually I had to surround the little remaining globules with my lips and suck it up.
Eventually I was done. Except for some leftover saliva, the platter was clean. I looked up at Ms. Daggett with pride.
“You’ve done the minimum expectation,” she said. It was hardly praise. That made me crave it all the more.
“Thank you,” I said automatically.
She laughed at me and I could feel the blood flushing to my face.
“You are a good little sub, aren’t you?” she asked mostly to herself.
“Yes,” I answered anyway.
The smile never left her face. She was beautiful even though she was too old for me. I noticed that her skirt had slipped up her thighs. I saw the top of her stockings. They were held up by garters.
Fuck.
She saw my gaze. The exposure of her skin had to be intentional. I only saw an inch of pale flesh between the top of the stocking and her skirt, but it was more than enough to get me hard again.
“You are a sub,” she proclaimed. “And probably a pervert too.”
I didn’t say anything. I didn’t disagree with her.
Ms. Daggett stood up from the edge of the table and hiked her skirt all the way up exposing more of her thighs. I could just spot the edge of her pink panties.
“You are a pervert,” she said before pulling her skirt all the way up.
I was disappointed that she was wearing her pink panties under her garter belt. There would be no easy way to remove them to get to her pussy. This was a dream come true. The black garters framed her shapely thighs and body perfectly. I wanted to rip her panties off her and bury my face in her pussy. Then I could die happy.
“Do you want to eat my pussy?” she asked me.
I almost cried with delight. “Yes! Please! I’ll do anything!”
“First take your hand off your cock. You don’t have permission to touch yourself.”
I had started jerking off again without realizing it. I yanked my hand away for fear of upsetting her further.
“I’m so sorry!”
She shook her head at me. “This will be a delight.” She could have told me to do anything right then and I would have. Ms. Daggett leaned back against her table and spread her legs. Her pink silk panties pulled tightly against her pussy.
“Eat me,” she said.
If I hadn’t cum a minute before I would have shot my spunk ten feet into the air. “Yes!” I cried eagerly crawling forward.
When my hands reached up to touch her thighs and hold her in place, she slapped me away.
“Just your mouth. Don’t touch me.” Her words were cruel and haughty. I loved it.
“Do you…do you want to take off your panties?” I was all but drooling. I was certain I could smell her damp, musky scent.
“No. Eat me through my panties. Make me cum or our entire deal is off.”
I could do that. I was certain of it. When you have a small cock, you learn to please women with your mouth and fingers.
I licked the expensive silk and got just a taste of her pussy. That was all I needed. The material was gossamer thin. When it got a little wet it clung to her skin. I quickly figured out she was well-groomed and there was no hair on her lips, maybe on her mound, but I wasn’t concerned with that body part at the moment.
I licked a second time and she moaned ever so softly.
I then started licking and sucking, seeking out her clit, finding it, sucking it through the silk. She leaned back further and braced herself with her arms on the edge of the table.
I continued on, using my tongue to force the silk into her tunnel, having the material outline her sex, concentrating on her clit.
I would have done this for hours if she had requested it. As it was, it only took me a few minutes to make her cum.
Her body trembled. She let out a little cry of passion. Her thighs closed on my head and squeezed and I was in Heaven.
All too soon her orgasm passed and she pushed me away from her.
“Get dressed,” she said while pulling down her skirt. She idly wiped the sweat from her brow with the back of her hand. “Take your contract. Read it. Sign it. Go back to your apartment. I’ll have someone drop by for the contract tomorrow.”
She turned her back to me and sauntered away. Maybe she was unsteady on her heels for a few steps, but then quickly recovered. She disappeared into a door on the far side of the room leaving me alone.
I quickly dressed and went to the elevator, pressing the button for my floor.
Chapter 3
When I got back to my apartment, the flood in the bathroom had been resolved. The carpet was slightly damp, but I didn’t see any major damage in my place. It all had to be in the place below.
Curious, I started reading the contract given to me by Ms. Daggett. It was written in legal language but was fairly straightforward. I’d essentially be her submissive sex slave for which I’d get a handsome monthly stipend. Essentially I would be an employee of her real estate company and I would have to do what she said.
After our morning’s little game, I was more than ready to do anything she asked me when it came to my cock or her pussy.
I should have read it more carefully.
I skimmed it.
I liked it.
I would have to do all sorts of humiliating sexual things for Ms. Daggett, my new mistress, and for that I would be paid. Where could this go wrong?
It even had a couple of safe words for me. One for a pause in the action, one to permanently end things. If I used the second one, I’d be fired from my so-called job.
That wasn’t going to happen.
I signed it because this was a dream come true.
Later in the afternoon when I was contemplating this positive turn in my life the bell to my door rang. Having nothing else to do I answered it.
There were three people there. An attractive redhead who was barely five feet tall. She wore a gray business suit and carried an expensive looking leather folder in one hand and briefcase in the other. Behind her were a man and a woman in maintenance staff uniforms for High Gate Tower. “I am Miss Eleanor Thomas,” said the redhead.
I smiled at her. I preferred blondes but redheads would do. I loved the freckles scattered across her nose and cheeks.
“Hello. How can I help you?”
She pushed by me into the apartment. The maintenance crew followed, carrying several heavy satchels and boxes.
“I work for Ms. Daggett. I believe you have some legal forms for me?”
I nervously went to the desk in the living room and picked up the contract giving it a final glance before handing it over to Eleanor. She checked to make sure I had signed on the dotted line on the last page and then shoved the contract into the leather folder.
It was at this point I noticed the other two were unboxing their equipment and were discussing what sounded like installation plans.
“What the hell are they doing?”
“Placing security cameras in your apartment, per your request,” Eleanor said with a smirk. “It shouldn’t take them long to finish the job.”
“Oh.” She stood in my living room watching the pair. “Don’t you need to get the contract for Ms. Daggett?”
Eleanor looked me up and down like a piece of meat. I sort of liked that and it caused my cock to stir.
“I do, but I need to make sure maintenance finishes their job first. Shall we sit down and discuss some details of your work and obligations to Ms. Daggett?”
Not knowing what else to do, I nodded yes.
We sat down at the dining table and Eleanor opened her briefcase, pulled out a plain manila folder, and placed it in front of her. From it she extracted a credit card. It already had my name on it.
“This is your credit card for incidental expenses. If you are going to charge something over five thousand dollars, you need to get approval first. Ten thousand is the monthly maximum.”
“How could I use that much—”
She plunged onward, ignoring my words. “You now have an active membership at Forward Thinking Gym. Here’s the address and schedule. You are expected to maintain your body to Ms. Daggett’s wishes.”
“Sure, okay, but—”
Next out of the briefcase came a brand new iPhone. “This is your new iPhone. You can keep your own, but this one is for Ms. Daggett to have private conversations with you. You might want to keep your old one for friends and family.”
“I suppose but—”
“You’ll continue to reside here so you’ll be available to Ms. Daggett at any point. You may not date anyone—male or female or otherwise—without Ms. Daggett’s express permission. You need to carry your new phone with you at all times so you can be tracked.”
“Wow, that’s…obsessive.”
Eleanor gave me a thin smile. “That’s the point. Let’s do an inspection of the cameras, shall we?”
The pair had worked fast. The cameras weren’t hidden, but they were small and subtle. They were in every room. Living room, kitchen, study, bedroom, bathroom. They started in the dining room as we left.
“They are on a Wi-Fi connection and are recording whenever the red light is on.” Eleanor indicated a small LED at one camera’s base. “When the blue is on, just the microphone is working. There are small speakers where Ms. Daggett can communicate with you.”
“Holy shit,” I breathed. “Will I have any privacy?”
“Of course not. You’re her sex slave.” Eleanor smirked at me again. “Is it worth it?” she asked me.
I couldn’t answer her. The maintenance crew finished, Eleanor signed their work order, and we were left alone.
“What next?” I asked, curious as to when I would be called upon to be humiliated by Ms. Daggett.
“This is my favorite part. Drop your pants.”
“What?”
“Drop. Your. Pants.”
“Am…am I supposed to do that? You said I wasn’t supposed to date anyone.”
“This isn’t a date.” She opened her briefcase and I saw a small selection of curved metal dicks. It took me a second to realize what I was seeing.
“Yes, male chastity cages,” she said brightly. “I need to find your correct size. Drop your pants.”
“But what about Ms. Daggett?”
“Do you really think I live and dream to put chastity cages on men I don’t know?” she asked me, exasperated. “I work for her. She wants this done. Let’s do it.”
I was delaying because I had more than just a vague sexual interest in Eleanor. The moment she revealed the cages to me, I immediately got hard.
Seeing as Eleanor was a strong older woman, I reluctantly and somewhat eagerly unbuckled my belt, unzipped my pants, and slowly pushed my pants down with my boxers.
I suppose she showed some professionalism by not bursting out laughing at my erection. However, she did scoff and shake her head.
“It’s cute,” she said, stretching out a hand and lightly touching the tip.
I had to stop myself from gasping at her touch.
Her words emasculated me. I loved that.
But my cock didn’t go down.
“Thanks?”
“It could be worse,” Eleanor said with a shrug of her shoulders. “I’ve seen smaller. I don’t know what it is with Ms. Daggett. She always finds men with the tiniest of cocks. I think we’ll start you with the second smallest.” The redhead pulled out a small metal birdcage in the shape of a flaccid cock along with a pair of scissors.
I danced away, protecting my small manhood. “What the fuck are you going to do with those?”
She proffered me the handles. “You need to trim your pubes. We’ll get you shaved later on, but short is fine for now.”
“Oh.” I was ashamed of my panic. The only thing to do was to take the scissors and start trimming. I did it right there in the dining room. I stood and she sat in a chair watching me.
The pile of dark blonde hair I left on the floor was more impressive than my cock.
She frowned when I was done. “There’s a problem,” she said, pointing.
I was still rock hard.
“I know.” I took a breath. “Let me go in the bedroom for a minute and I’ll jerk off and go soft.”
Eleanor emphatically shook her head. “No. You don’t get to do that any longer. Wait here.”
She stood up and went to the kitchen. She returned a minute later with a baggie full of ice cubes.
“No!” I protested.
“Then go soft right now because this cage is going on your cock before I leave here.”
I couldn’t do it. I thought of my grandmother. Of dead puppies. Of baseball. I hated baseball. I still didn’t go soft.
Eleanor pressed the ice to my cock and balls and a minute later I was sufficiently soft.
The cage was perfectly engineered to accomplish its one task: to keep cocks from getting hard.
After applying a bit of lube to my cock and balls, she forced my sac through the base ring and then my shaft. The ring wasn’t too tight, but I could feel it. The curved shaft went over my shaft. My head just barely reached the end of the little cage. The whole thing was held together and sealed with a small brass padlock.
When she snapped it shut my cock wanted to get hard right away.
“I need to take a picture of you for Ms. Daggett,” said Eleanor.
“What?” I was in panic mode. I couldn’t get to my cock.
What the fuck was wrong with me!? Why did I let this happen?!
Before I could react, Eleanor pulled out her cell phone and snapped several pictures of me, half-naked and wearing a chastity cage.
I wanted to cry.
“What the fuck are you doing?”
Eleanor was amused at my reaction. “Just documenting that I’m doing my job. Ms. Daggett would be unhappy if I didn’t have you in your cage by now.” She fiddled with her phone for a moment while I stood there, my pants around my ankles, my shirt pulled up to keep it out of the way while she worked, a metal chastity device on my cock. I felt humiliated.
It turned me on too.
After a moment, she put her phone away and displayed a pair of small keys to me. “Very good. Now, I’m giving one key to Ms. Daggett. The other will go to the security desk in the lobby. If you ever need an emergency removal, just ask whoever is there for box 78. It’ll be logged and Ms. Daggett will know that you’ve used it.”
My mind wasn’t fully functioning. I was staring at my trapped cock. I loved and hated it.
“One final thing before I go,” she said. When I looked at her she reached behind her back and unzipped her skirt before dropping it to the floor. “Ms. Daggett said you had a talented tongue. She wanted my opinion.”
I looked at the lacy green panties she was wearing. She had them over the garters that held her stockings up. My cock tried to stiffen and the pain was…exquisite.
Chapter 4
“You want me to…”
I couldn’t voice what she wanted me to do, even though I desperately wanted to do it.
Eleanor rolled her green lace panties down her hips and thighs. She artfully lifted one leg to free herself from the intimate article of clothing, but it remained tangled around one ankle. I only briefly noted this because my eyes went right to her pussy.
It was beautiful. She was a natural redhead, which I had already guessed based on her coloring and freckles, but it was nice to see it confirmed with the little landing strip of dark red hair decorating her mound.
We were still in my dining room area. She was perched on the edge of a chair with her legs spread.
As if it wasn’t obvious, she said, “I want you to eat my pussy. If you do a good job, I’m sure Ms. Daggett will reward you. If you don’t do a good job…” She paused and smiled and licked her lips. “She said I could punish you.”
Both of those results excited me.
I took a good look at Miss Eleanor Thomas again. Natural redhead. Scattering of freckles. Even though she was sitting down, I knew she was short. Maybe five foot two at most. I judged her tits to be on the small side; that was fine. I had stolen a few glances at her ass while we had walked through my apartment. Maybe it was a bit too big for my taste, but no one in their right mind would complain about it.
I had waited too long. “Get to work,” she ordered me, pointing at her pussy.
It seemed insane that I was going to eat two women’s pussies on the same day, but it was the only thing going right in my life.
I crawled forward. I knew how she wanted me to act. Still sitting on the edge of the chair, she spread her legs wide for me. I took a risk and wrapped my arms around her thighs. Unlike Ms. Daggett, she didn’t complain.
She moaned a little when I licked her pretty pink pussy and quickly found her clit.
“Keep going,” she encouraged me breathily.
I glanced up to see that she was looking down at me. I closed my eyes and got to work.
Either Eleanor was deprived when it came to sex or she really liked her job with Ms. Daggett. Her pussy was already wet when I pressed my nose into her fiery pubic curls. Her squirming and breathing response told me everything I needed to know.
Of course, I had no way of knowing if what she told me was the truth or not. It didn’t matter. I had already completely fucked up my life.
While I was eating her out, my cock periodically tried to get hard, but the cage prevented it. It sort of hurt, but it was fine. I went soft again right away. In any case, I was too distracted by trying to please Eleanor than I was about getting off myself.
It didn’t take terribly long to bring Eleanor to orgasm. Maybe five minutes. She gasped and cried out as I tongued her clit, sucking it to get her over the edge.
She left a wet streak on my dining room chair.
After her moment of crisis passed, she sucked in several deep breaths and giggled. “Oh, I’ll have a good report to give Ms. Daggett,” she said as she pushed me away and pulled her panties back into place.
“So…I passed?” I asked, still crouched on the floor. I wiped my face with the back of my hand. She hadn’t exactly squirted but Eleanor wasn’t exactly stingy when it came to amrita.
She just shrugged and picked up her skirt, pulling it up her legs and zipping it up with a practiced hand. “We’ll see. Don’t go anywhere the rest of the day. Ms. Daggett may have need of you.”
I just nodded and watched as she let herself out of the apartment. Maybe I had been wrong about her ass.
I reviewed the material that Eleanor had left behind. That is, I glanced at it and wondered what the hell I had gotten myself into.
Not knowing what else to do, I took a shower. Maybe it was to wash away the shame, but I used the opportunity to see how difficult it would be to get the cage off my cock.
I discovered it would certainly be possible. In the cold water my cock shrank alarmingly and I realized that I would be able to pull out of the shaft and then it would be fairly simple to push everything back through the base ring.
The downside to this was that it would be incredibly difficult to get it back on.
I wanted it on and I wanted it off. How fucked up is that.
I left it on. I wanted to please Ms. Daggett when I saw her again. Maybe this was a fucked up game, but if she was promising me real money, I’d be happy to be her whore for a few weeks.
Maybe a couple of months.
Could I do it for a year?
Forever?
I also figured out that it wouldn’t be that difficult to cut the lock off if I wanted. I didn’t have a pair of bolt cutters, but they could easily be bought at a hardware store.
I’m sure that would piss off Ms. Daggett.
As I walked around my apartment I discovered that the weight of the cage, though minimal, was definitely there, tugging at me. I sort of liked it, but after an hour I realized that boxers weren’t going to cut it. Digging into my somewhat limited clothing stash, I found the briefs I wore to the gym. Those gave me the support I needed.
I was bored in my apartment, but I was too afraid to leave. Eventually I got hungry and decided to make some dinner. Bachelors don’t generally cook for themselves so my options were limited. My grilled cheese was half done when the doorbell rang.
I was certain it was Ms. Daggett coming to offer to humiliate and then fuck me.
I was disappointed when it was a security staff I had never seen before. He was holding two boxes.
“These are for you,” he grunted unnecessarily and had me sign some form on his clipboard.
I had no sooner closed the door and was about to open the boxes when Ms. Daggett’s voice filled my apartment.
“These are replacements for what you lost.”
I looked at the camera recently installed. The blue light was on. Her people worked fast.
“What are they?” I stupidly asked.
“Open them.” She sounded annoyed. I didn’t blame her.
Working quickly I found she had delivered to me a new laptop and an Xbox better than the one that had been stolen from me.
“You know that I’ll be monitoring everything you use these for, don’t you?” she asked me over the speakers.
“Yes. Of course.” I was floored at how quickly she had worked for my pleasure.
“And take off your clothes,” she added. “When you’re alone, I want you naked…except for your cage.”
“Sure. Anything you want.”
The blue light on the camera winked off to red. Was it only on when she talked to me? Was it recording everything I did?
Just to be safe, I stripped off my clothes and then proceeded to hook up the Xbox to the television and set up the laptop.
Using my two new toys was the rest of my night.
When I got into bed, naked but for the cage, it was the worst night of my life.
Chapter 5
It felt strange going to sleep with a cage on my cock, but I just thought of it like wearing a cast or some new jewelry. It was fine…until I woke up in the middle of the night with an incredible pain in my crotch because I was getting hard and the cage was stopping it.
Fuck.
Fuck it hurt!
I crawled out of bed, went to the freezer, and got some ice to make myself go soft.
It took what felt like hours for it to go back to normal.
I wasn’t sure I could do this. No way was I going to be able to wear a metal chastity cage on my dick for the rest of my life.
But I was too worried about my financial future to really take it off.
It took me an hour to go back to sleep.
I woke up at some ungodly hour because I developed morningwood and needed to piss.
Fuck!
There was light coming in through the blinds and I stumbled to the bathroom. I couldn’t get soft enough to piss and my bladder was full. Fuck and fuck!
Back to the kitchen, more ice. I got soft enough to pee, but had forgotten that the night before I had pissed while sitting down so I wouldn’t make a fucking mess.
I made a fucking mess with the cage on. Piss everywhere. I couldn’t stop because it was the only physical pleasure I was getting from my dick.
I pissed all over the bathroom floor. My bathroom was taking a beating lately. Only half my piss went in the toilet. I cleaned up the best I could with paper towels and took a shower.
A cold shower.
Just as I was getting dressed, the speakers went on again.
“Report to my office at nine a.m.” Immediately after Ms. Daggett was done speaking the blue light changed to red.
I had plenty of time. I dressed up a bit. Button down shirt. Dress pants. Blazer. No tie. Keeping it casual. A clean pair of briefs to support my cage.
In the packet that Eleanor had left was a key to the elevator for the twenty fourth floor. I used it to access Ms. Daggett’s office.
The moment I stepped off the elevator she saw me and narrowed her eyes.
“Stop right there.”
I froze in place.
“Strip,” she ordered, a smile on her face. Whatever work she was doing she set aside and propped her chin on her hands, watching me closely.
I had no idea if we were alone or not.
I didn’t care.
I stripped.
I didn’t make a big show of it, but did so carefully and precisely, setting my clothes on a small table next to the elevator that was definitely set there for just that purpose.
When I was down to my briefs, she stopped me again. “Those are terrible. Don’t ever wear them again.”
I looked down. They were just athletic briefs, but she was the boss. I pulled them down and set them on the pile. I was ashamed to be wearing my cock cage and nothing else.
That’s why my small cock tried to get erect. My mind was fucked up.
“Approach,” she said.
I did so, stopping a few feet in front of the table she used for a desk.
Ms. Daggett stared at me for a minute before getting up. Today she had her hair pulled back into a practical bun and wore a pinstriped pantsuit with a red blouse. I wanted to see her naked but I knew the rules. She was in charge.
I liked being naked in front of her when she was in charge.
She stood up and walked around the desk and then around me, admiring my body.
“Very nice,” she said. “The cage suits you. You know that you’re expected to maintain your body, correct?”
“Yes ma’am,” I said smartly.
Her hand lashed out and smacked me on the ass. I gasped a little in shock. It didn’t really hurt, but it surprised me.
“Yes mistress,” she corrected me. “Not ma’am. If we are in public you can call me Ms. Daggett, but never use my given name.”
“Yes mistress,” I said. Her game, her rules.
“I like the suit you wore here. You have good taste. But the underwear is wrong for you. You will also need to do something about your body hair.”
I looked down at myself. I’m not hairy. A little on the chest. My trimmed pubes. The treasure trail to it. Average hairiness of legs.
“What do you want me to do about it?” I asked stupidly.
“We’re going to remove it,” she said, practically licking her lips.
I shivered at the thought of using a razor on myself but then her hand was curling around my balls and the cage that held my shaft.
“How was your night?”
“Terrible, mistress. I had a lot of trouble sleeping with…this…on.”
“I’m not surprised. You’ll get used to it. Miss Thomas gave me an excellent report on you.”
I was puzzled. “Miss Thomas. Oh, you mean Eleanor.”
This time her slap was across my face. It stung. Clearly she had a sadist streak in her.
“You’ll refer to her as Miss Thomas from now on. You already know to address me as Ms. Daggett. I knew that you already know my given name. Never use it. If you do…well, we’ll see what your tolerance for pain is. It would be best if you just forgot my given name.”
“Yes, mistress. I’ll remember that, mistress.”
“You’re a quick learner. I like that.”
She pulled her other hand away from my cock and stepped back. “Now for your reward.”
Ms. Daggett turned her back to me and let her jacket slide down her arms. Setting it aside, she then unbuttoned her pants and pulled them, along with her underwear, down her legs.
I was treated to her perfectly sculpted ass.